Process of producing explosive compounds and product thereof



UNITED STATES PATENT OFFICE.

CHARLES M. STINE, OF WOODBURY, NEW JERSEY, ASSIGNOR TO E. I. nU PON'I DE NEMOURS AND COMPANY, OF WILMINGTON, DELAWARE, A CORPORATION OF DELAWARE.

PROCESS OF PRODUCING EXPLOSIVE COMPOUN'DS AND PRODUCT THEREOF.

l 3,()9,551 Np Drawing.

To all whom it may concern:

Be it known that I, CHARLES M. STINE, of W oodbury, in the county of Gloucester, and in the State of New Jersey, have invented a certain new and useful Improvement in Processes of Producing Explosive Compounds and Products Thereof, and do hereby declare that the following is a full, clear, and exact description thereof.

My invention relates particularly to a process for producing explosives of an advantageous character, and the product thereof. The object of my invention is to provide a process for producing explosives and particularly explosive compounds containing a nitro group and a nitrate group, or a plurality of such groups, and the product produced thereby. More particularly, the object of my invention is to provide a process of producing explosive compounds containing a plurality of nitro groups and a plurality of nitrate groups. A further object of my invention is to provide compounds of this character in which a nitro group is located in the ring and a nitrate group is located in the side chain of the compound. I have found that of these compounds dinitrotolylene nitrate is a particularly advantageous product.

While my invention is capable of embodiment in many different forms, for the purpose of illustration I have described only certain forms thereof. For example, I may proceed as follows The compound produced in accordance With my process may be, for example, any one of the following:

But, as I have pointed out above, I have found that dinitrotolylene-nitrate is a particularly valuable product. In carrying out my process xylol may be chlorinated in direct sunlight at about a temperature of 100 C. the flow of chlorin being continued until a theoretical increase in Specification of Letters Patent.

Patented July 8, 1919.

Application filed July 20, 1916. Serial No. 110,278.

weight has been attained corresponding to the di-chlor derivative. When the mixture has cooled down a mass of crystals separates out, which consist of phenyl-paradimethylchlorid. These crystals are filtered oil and nitrated by applying a mixture of nitric and sulfuric acids according to the pro cedure usually followed in nitration, preferably until the dinitro compound is obtained. The nitrated material is heated with pure Water under a pressure of preferably 20 pounds per square inch, until the chlorin atoms in the side chain have been replaced by hydroxyl groups. The aqueous solution is then evaporated to drive off the water and hydrochloric acid, and the dinitro henylparadimethylol is obtained in wel crystallized form. The dinitrophenylparadimethylol is nitrated further by the application of a mixture of sulfuric and nitric acids in accordance with the procedure usually followed in nitration. A White crystalline material is thus obtained, which can be filtered from the mixed acids, Washed and neutralized. and which, after drying, is suitable for use as an explosive, or as an ingredient in explosives. The explosive thus obtained is exceedingly powerful and very stable.

Such compounds may also be prepared by other processes, as, for example, nitration of an aromatic hydrocarbon to the mono-, dior tri-nitro compound, chlorination of the dinitro compounds to introduce chlorin into the side chain, hydrolysis of the chlor-nitro compound to produce a nitro hydroxyl compound and nitration of the nitro-hydroxyl compound to produce a nitro nitrate.

While I have described my invention above in detail, I wish it to be understood that many changes may be made therein Without departing from the spirit of my invention. For example, I do not Wish to limit myself to any particular method of preparation, and I wish it to be understood that the compounds produced in accordance with my invention may be used as such or in mixtures of various kinds, as desired.

I claim- 1. A process of producing an explosive compound which comprises nitrating and halogenating an organic compound to introduce a nitro group and a halogen, hydrolyzing' to substitute a hydroxyl group for the halogen, and nit rating to sul'istitut c a. nitrate group for the hydroxyl roup.

2. A process of producing an (.XplflSlVU compound which comprises nitrating and balogenating a hydrocarbon to introduce a nitro group and a halogen, hydrolyzing to .slllist itutc a hydroxyl group tor the l'uilogen and nitrating to substitute a nitrate group for the hy 'droxyl group.

it. A process of producing an explosive compound \Vllii'll comprises nitrating and halogcnating an aromatic hydrocarbon to introdure a nitro group and a halogen, by drolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group.

4. A process which con'iprises nitrating and halogcnating Xylol to introduce a nitro group and a halogen, hydrolyzing to sub stitutc a lrvdroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group.

5. A process Which comprises nit-ruling and halogenating an organic compound to introdure a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group i or the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the halogenation being continued until the dihalogen derivative is obtained.

(3. A. process which comprises nitrating and halogenating a hydrocarbon to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen. and nitrating to substitute a nitrate group for the hydroxyl group, the halogenation being continued until the (ii-halogen derivative is obtained.

7. A process which comprises nitrating and halogenating an aromatic hydrocarbon to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the halogenation being continued until the dihalogen derivative is obtained.

8. A process which comprises nitrating and halogenatin Xylol to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the halogenation being continued until the (ii-halogen derivatire is obtained.

9. A process which comprises nitrating and halogenating an organlc compound to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the initial nitration being continued until the dinitro compound is produced.

10. A process which comprises nitreting and halogenating a hydrocarbon to introduce :1 nitro group and a halogen, hydrolyzing to substitute lrydroxyl group for the halogen, and nitrating to substitute a nitrate grou for the hydroxyl group, the initial nitration being continued until the dinitro compound is produced.

11. A process which comprises nitrating and halogenating an aromatic hydrocarbon to introduce a nitro group and a halogen,

hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the initial nitration being continued until the dinitro compound is produced.

12. A process which comprises nitrating and halogenating xylol to introduce a nitro group and a halogen, hydrolyzing to sub stitnte a hydroxyl group for the halogen. and nitrating to substitute a nitrate group for the hydroxyl group, the initial nitra tion being continued until the dinitro com pound produced.

13. A iirocrss of producing an cxplosiie compound which comprises nitrating and halogennting an organic CUIHPUHIHl to in troduce :1 nitro group and a halogen, by drolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group i or the hydroxyl group, and the halogenation being carried out before the initial nitration.

14. A process of producing an explosive compound which comprises nitrating and halogenating a hydrocarbon to introduce :1 nitro group, and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group and the halogena tion being carried out before the initial nitration.

15. A process of producing an explosive compound which comprises nitrating and halogenating an aromatic hydrocarbon to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the l'ialogen. and nitrating to substitute a nitrate group for the hydroxyl group, and the halogenation being carried out before the initial nitration.

16. A process which comprises nitrating and halogenating xylol to introduce a nitro group and a halogen, hydrolyzing to sub stitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, and the halogenation being carried out before the initial nitration.

17. A process which comprises nitrating and halogenating an organic compound to introduce a. nitro group and a halogen, hydrolyzing to substitute a hydroxyl group till for the halogen, and nitrating to substitute gcnation being carried out before the initial nitration.

18. A process which comprises nitrating and halogenating a hydrocarbon to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl roup for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the halogenation being continued until the di halogen derivative is obtained, the halogenation being carried out before the initial nitration.

19. A process Which comprises nitrating and halogenating an aromatic hydrocarbon to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroXyl group, the halogenatlon being continued until the dihalogen derivative is obtained, the halogenation being carried out before the initial nitration.

20. A process which comprises nitrating and halogenating xylol to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the halogenation beino' continued until the di-halogen derivative 1s obtained, the halogenation being carried out before the initial nitration.

21. A process which comprises nitrating and halogenating an organic compound to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the initial nitration being continued until the dinitro compound is produced ,the halogenation being carried out before the initial nitration.

22. A process which comprises nitrating and halogenatiug a hydrocarbon to introduce a nitro group and a halogen, hydro lyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for a hydroxyl group, the initial nitration being continued until the dinitro compound is produced, the halogenation being carried out before the initial nitration.

23. A process which comprises nitrating and. halogenating an aromatic hydrocarbon to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the initial nitration being continued until the dinitro compound is produced, the halogenation being carried out before the initial nitration.

24. A process which comprises nitrating and halogenating xylol to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and

nitraling to substitute a nitrate group for the hydroxyl group, the initial nitration being continued until the dinitro compound is produced, the halogenation being carried out before the initial nitration.

25. A process Which comprises nitrating and halogenating an organic compound to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the halogenation being continued until the dihalogen derivative is obtained, both of the halogens being substituted by hydroxyl groups, the initial nitration being continued until the dinitro compound is produced.

26. A process which comprises nitrating and halogenating a hydrocarbon to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroxyl roup for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the halogenation being continued until the di-halogen derivative is obtained, both of the halogens being substituted by hydroxyl groups, the initial nitration being continued until the dinitro compound is produced.

27. A process which comprises nitrating and halogenating an aromatic hydrocarbon to introduce a nitro group and a halogen, hydrolyzing to substitute a hydroXyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the halogenation being continued until the di halogen derivative is obtained, both of the 00 halogens being substituted by hydroxyl groups, the initial nitration being continued until the dinitro compound is produced.

28. A process which comprises nitrating and halogenating Xylol to introduce :1 nitro 5 group and a halogen, hydrolyzing to substitute a hydroxyl group for the halogen, and nitrating to substitute a nitrate group for the hydroxyl group, the halogenation being continued until the (ii-halogen derivativc is obtained, both of the halogens being substituted by hydroxyl groups, the initial nitration being continued until the dinitro compound is produced.

29. An explosive containing an organic compound having therein a nitro group and a nitrate group, there being a plurality of one of said groups present.

30. An explosive containing an organic compound of the aromatic series, having therein a nitro group and a nitrate group, there being a plurality of one of said groups present.

31. An explosive containing an organic compound of the aromatic series having side chains and having a plurality of nitro groups in the ring and a plurality of nitrate groups in the side chains.

32. An explosive containing an organic compound of the aromatic series having side chains and having two nitro groups in the ring and two nitrate groups in the side chains.

33. An explosive containing an organic compound having a plurality of nitro groups and a plurality of nitrate groups.

34. An explosive containing an organic compound of the aromatic series having therein a plurality of nitro groups and a plurality of nitrate groups.

35. An explosive containing an organic compound of the aromatic series having side chains and having two nitro groups and two nitrate groups.

36. An explosive containing an organic compound of the aromatic series having therein two nitro groups and two nitrate groups.

37. An explosive composition containing an organic compound having therein a nitro group and a nitrate group, there being a plurality of one of said groups present.

38. An explosive composition containing an organic compound of the aromatic series, having therein a nitro group and a nitrate group, there being a plurality of one of said groups present.

39. An explosive composition containing an organic compound having a plurality of nitro groups in the ring and a plurality of nitrate groups in the side chains.

40. An explosive composition containing an organic compound of the aromatic series having side chains and having two nitro groups in the ring and two nitrate groups in the side chains.

41. An organic compound of the aromatic series having the formula O H (CH NO (N0 In testimony that I claim the foregoing I have hereunto set my hand.

CHARLES M. STINE. Witnesses:

FRANK L. Porn, WM. G. Loner.

Copies of this patent may be obtained tar five cents each, by addressing the Commissioner of Patents, wellington, ID. 0. 

